Cysteamine → 4-Bromo-3-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide
Reaction equation
[Br:1][C:2]1[C:3]([CH2:7]Br)=[N:4][S:5][CH:6]=1.[NH2:9][CH2:10][CH2:11][SH:12]>>[BrH:1].[Br:1][C:2]1[C:3]([CH2:7][S:12][CH2:11][CH2:10][NH2:9])=[N:4][S:5][CH:6]=1Participants
Procedure
The reaction of 4-bromo-3-(bromomethyl)isothiazole (8.5 g.) with cysteamine (from cyteamine hydrochloride, 3.76 g.) was performed under conditions similar to those described in Example 121. From the reaction there was obtained 4-bromo-3-[(2-aminoethyl)thiomethyl]isothiazole hydrobromide, which, following recrystallisation from ethanol-ether and acetonitrile, gave needles (4.05 g.) m.p. 111°-112°. The amine base (2.73 g.) was isolated by basification with sodium hydroxide and extraction with chloroform and then dissolved in ethanol and treated with methyl isothiocyanate (0.78 g.). The solution was heated under reflux for 30 minutes, concentrated and the residue triturated with ether to yield the crystalline thiourea (2.9 g.) m.p. 60°-61°. Recrystallisation from isopropyl acetate gave N-methyl-N'-[2-((4-bromo-3-isothiazolyl)methylthio)ethyl]thiourea (2.3 g.) as needles, m.p. 62°-63°.
Workup
- customFrom the reaction there
Sources & evidence
- ORD record
- ord-ff3f3e2f9f214b90ad10c1bf8d7a716c
- Source dataset
- uspto-grants-1981_10
- Patent number
- US04293699
Reaction notes
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